Pd-Catalyzed Enantioselective Heck Reaction of Aryl Triflates and Alkynes

被引：72
|
作者：
Zhu, Chenghao [1 ]
Chu, Haoke [2 ]
Li, Gen [2 ]
Ma, Shengming [2 ]
Zhang, Junliang [1 ,2 ]
机构：
[1] East China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, 3663 North Zhongshan Rd, Shanghai 200062, Peoples R China
[2] Fudan Univ, Dept Chem, Shanghai 200438, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2019年 / 141卷 / 49期
关键词：
BETA-HYDRIDE ELIMINATION; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; CHIRALITY TRANSFER; TETRASUBSTITUTED ALLENES; PROPARGYLIC PHOSPHATES; ESTERS; CYCLIZATION; ALLYLATION; ALLENOATES;
D O I：
10.1021/jacs.9b10883
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first palladium-catalyzed asymmetric Heck reaction between aryl triflates and alkynes to give trisubstituted allenes with high er under mild reaction conditions is described. The key to the success is the discovery and fine-tuning of the different N-substituents of Xu-Phos, which ensure the enantioselectivity and reactivity. Synthetic transformation of the chiral allenes with high chirality transfer was also demonstrated.
引用
收藏
页码：19246 / 19251
页数：6
相关论文
共 50 条
  • [1] Pd-Catalyzed Enantioselective Double Heck Reaction
    Ju, Baihang
    Chen, Shigui
    Kong, Wangqing
    [J]. ORGANIC LETTERS, 2019, 21 (23) : 9343 - 9347
  • [2] Synthesis of Enantioenriched Trisubstituted Allenes via Pd-Catalyzed Heck Reaction of Alkynes
    Hou, Xuelong
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (06) : 1800 - 1801
  • [3] Pd-catalyzed fluorination of (hetero)aryl halides and triflates
    Milner, Phillip
    Buchwald, Stephen
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [4] Pd-Catalyzed Difluoromethylthiolation of Aryl Chlorides, Bromides and Triflates
    Wu, Jiang
    Lu, Changhui
    Lu, Long
    Shen, Qilong
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (11) : 1031 - 1034
  • [5] Palladium-Catalyzed Asymmetric Heck Coupling of Aryl Triflates and Alkynes
    Cai, Yuan
    Shi, Shi-Liang
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (03) : 810 - 811
  • [6] Ligand rearrangement and modification in the Pd-catalyzed fluorination of aryl triflates
    Milner, Phillip J.
    Maimone, Tom J.
    Buchwald, Stephen L.
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
  • [7] Pd-Catalyzed Conversion of Aryl Chlorides, Triflates, and Nonaflates to Nitroaromatics
    Fors, Brett P.
    Buchwald, Stephen L.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (36) : 12898 - +
  • [8] Enantioselective Intermolecular Heck and Reductive Heck Reactions of Aryl Triflates, Mesylates, and Tosylates Catalyzed by Nickel
    Huang, Xiaolei
    Teng, Shenghan
    Chi, Yonggui Robin
    Xu, Wenqiang
    Pu, Maoping
    Wu, Yun-Dong
    Zhou, Jianrong Steve
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (06) : 2828 - 2832
  • [9] Pd-catalyzed enantioselective intramolecular Heck reaction to access disubstituted dihydroisoquinolinone with a terminal olefin
    Li, Sanliang
    Chen, Qiaoyu
    Zhang, Zhan-Ming
    Zhang, Junliang
    [J]. GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (04): : 374 - 376
  • [10] An Improved Catalyst System for the Pd-Catalyzed Fluorination of (Hetero)Aryl Triflates
    Lee, Hong Geun
    Milner, Phillip J.
    Buchwald, Stephen L.
    [J]. ORGANIC LETTERS, 2013, 15 (21) : 5602 - 5605
12345